10 Movie Womanizers, From the Sick to the Sublime

The movies are full of bed-hopping men — think of Humphrey Bogart's serial flirtations in The Big Sleep (1946), and Richard Roundtree laying his way uptown and down in Shaft (1971). But in Steve McQueen's Shame, womanizing is not just an outgrowth of the plot — it is the plot. And it's just the latest example of a sub-genre we'll call the Lothario film. Particularly plentiful since the Sexual Revolution, Lothario films are the pictures that deal with men tripped up on their own swinging dicks. Here, fond memories of our favorite dicks and the collateral damage they left in their wakes.

Alfie (1966)

Director: Lewis Gilbert

Lothario: Michael Caine

In the year of Blow-Up, as David Hemmings wrestled with models in hip Notting Hill, Alfie offered a look at sex among the working class in a resolutely unsexy Swinging London. Wearing a slack expression and reciting his nihilist philosophy to the camera in aitch-dropped Cockney, Michael Caine's Alfie is perhaps the most boorish womanizer on this list: lofty and bullying with his mistresses, depending on his stallion-like physical presence alone to keep them satisfied. Featuring a dismal illegal abortion scene, it's a time-capsule of the moment just before sex and consequences were parted.

Play Misty for Me (1971)

Director: Clint Eastwood

Lothario: Clint Eastwood

Clint Eastwood has produced a long line of out-of-wedlock children and films since '71; this was the first of the latter. Misty examines the hazards of free love, with Clint playing a DJ whose on-air whisper keeps the sheets hot at his Carmel-by-the-Sea bachelor pad, until one casual lay (Jessica Walter) first refuses to take the hint, then comes back with a knife. A "Hell hath no fury" film that inverts assumptions about masculine predators and feminine victims.

Shampoo (1975)

Director: Hal Ashby

Lothario: Warren Beatty

Warren Beatty co-wrote the screenplay with Robert Towne and, bouncing between L.A. trysts on his motorcycle, starred as hairdresser George Roundy. The opposite of aggressive bluster, Beatty's reserved, shy, withholding performance is a lovely tiptoe approach — his whisper is what draws the women closer. If George is ultimately as fleeting and impossible to hold as the Santa Ana wind, he also is granted a measure of heroism amid a rising tide of materialism: "I don't fuck for money. I do it for fun."

Fellini's Casanova (1976)

Director: Federico Fellini

Lothario: Donald Sutherland

Fellini's favorite theme was the attrition of la dolce vita, and he was given a natural subject in the person of Giacomo Girolamo Casanova, Venetian-born diarist and legendary cocksman. Per the libido-tormented director, Casanova was "the evil version of the Italian male . . . a sinister Pinocchio who refuses to turn into a well-behaved boy." "Donaldino" Sutherland plays Casanova as a sexual automaton humping across what Fellini called his "electrical wax museum" of 18th-century Europe, constructed in Cinecittà studios.

The Man Who Loved Women (1977)

Director: Franois Truffaut

Lothario: Charles Denner

Charles Denner, funny in his desperate, intent pursuits, plays Bertrand Morane, a Montpellier engineer described by one of his mistresses as "the wolf with a worried look," who decides to write the story of his life. A lesser-known late masterpiece, Truffaut's film is a swirl of questions about the paradoxes of sex, such as: "Was it possible to find pleasure without hurting someone?" with a wonderful framing device that dares to suggest that a Don Juan might be fondly remembered rather than regretted.

The Pick-up Artist (1987)

Director: James Toback

Lothario: Robert Downey Jr.

James Toback's own trawling has been widely rumored — in a 1989 foldout chart in Spy and the pages of Gawker besides. Otherwise, Toback is probably best known as the director of Fingers and as the wingman to pal Warren Beatty, this film's shadow producer, who once summed up his might-as-well-ask seducer's credo thusly: "You get slapped a lot, but you get fucked a lot, too." Pick-up Artist doubles down on the playing-the-odds metaphor, with a spaniel-eyed Robert Downey (before he had his gap-teeth closed and when there was still a vulnerability beneath the glibness) as the skirt-chaser who reinvents himself for every new pickup.

Boomerang (1992)

Director: Reginald Hudlin

Lothario: Eddie Murphy

Playing an infamous Manhattanite lady-killer, Eddie Murphy is too eager to have the audience on his side to make Boomerang's player-who-gets-played comeuppance plot go, but on the way to wholesome yawn Halle Berry, he passes through quite a menagerie of actresses, including mewling senior Eartha Kitt, finishing-school freak Robin Givens, and Amazonian Grace Jones.

Deconstructing Harry (1997)

Director: Woody Allen

Lothario: Woody Allen and loads of alter egos

You need only look at Liam Neeson's spooked "What have I gotten myself into?" expression in every scene in Husbands and Wives (1992) to realize there is a world of darkness on the fringes of every Allen comedy, and most of it is blackly disgorged here. Allen's Harry Block, a philandering novelist who shtups his sister-in-law and fashions a book from it, is his most unpleasant alter ego, with the film an erotomaniac's self-revelation to rival Robert Crumb's My Troubles with Women.

Auto Focus (2002)

Director: Paul Schrader

Lothario: Greg Kinnear

Auto Focus is a love story of a sort, about the symbiotic ante-upping relationship that develops between A/V geek John Carpenter (Willem Dafoe) and Hogan's Heroes star Bob Crane (Greg Kinnear), who embark together on an odyssey of amateur porn and group gropes that only ends when Crane shows up in a Scottsdale motel room, bludgeoned to death with a tripod. Saddled with a laughable formal "hook" — as Crane's life goes out of control, so does the camerawork — Auto Focus works best as outright farce of sexual desperation, as in the scene of increasingly spooked-looking Crane switching a bar TV to Heroes — like Sutherland's Casanova imitating his own flyleaf portrait — when he's doing his evening's cruising.

Sideways (2004)

Director: Alexander Payne

Lothario: Thomas Haden Church

A dialogue between fidelity and inconsequentiality, connoisseurship and appetite, Sideways' two poles are represented by Paul Giamatti's Miles and Thomas Haden Church's aging soap-opera stud, Jack. "There are some things that I have to do that you don't understand. . . ." says Jack, in a voice that speaks of surrendered self-control and the dilemma of a sex drive without a brake: The Guy Can't Help It.